N-allyl-2-hydroxy-6-phenylpyrimidine-4-carboxamide | 1328915-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-allyl-2-hydroxy-6-phenylpyrimidine-4-carboxamide
• 英文别名: 2-oxo-4-phenyl-N-prop-2-enyl-1H-pyrimidine-6-carboxamide
• CAS: 1328915-36-1
• 化学式: C₁₄H₁₃N₃O₂
• 分子量: 255.276
• InChiKey: VSYAADNHZHIFBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-hydroxy-2-oxo-4-phenylbut-3-enoic acid 在 硫酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.5h， 生成 N-allyl-2-hydroxy-6-phenylpyrimidine-4-carboxamide
  参考文献：
  名称：

  SYNTHESIS AND AChE INHIBITING ACTIVITY OF 2, 4 SUBSTITUTED 6-PHENYL PYRIMIDINES

  摘要：

  Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification of I-A, followed by reaction with benzyl or allyl amines in the presence of TBTU yielded 2-hydroxy-6-phenyl-pyrimidine 4-carboxamides. AChE and BuChE assays revealed 2-hydroxy-6-phenyl-pyrimidine-4-carboxyallyamide as the most active compound, IC50=90 mu M, with no inhibition of BuChE.

  DOI：

  10.4067/s0717-97072012000300020

文献信息

• SYNTHESIS AND AChE INHIBITING ACTIVITY OF 2, 4 SUBSTITUTED 6-PHENYL PYRIMIDINES
  作者：CRISTIAN PAZ、MARTIN G PETER、BERND SCHMIDT、JOSE BECERRA、MARGARITA GUTIÉRREZ、LUISA ASTUDILLO、MARIO SILVA

  DOI：10.4067/s0717-97072012000300020

  日期：——

  Novel substituted pyrimidines were synthesized from methyl 2,4-dioxo-4-phenyl-butanoate (I-A) and urea, followed by Mitsunobu coupling of I-A with benzyl or allyl alcohol to give the corresponding 2-hydroxypyrimidine ethers in good yields. Saponification of I-A, followed by reaction with benzyl or allyl amines in the presence of TBTU yielded 2-hydroxy-6-phenyl-pyrimidine 4-carboxamides. AChE and BuChE assays revealed 2-hydroxy-6-phenyl-pyrimidine-4-carboxyallyamide as the most active compound, IC50=90 mu M, with no inhibition of BuChE.